The Completely Audacious Guide to Breaking the Ice

Growing up, I had a severe speech impediment. I had an especially hard time with words that began with the letter “m.”

My name is Michael. As you might imagine, I was terrified of meeting new people.

I got over it by taking a sales job. Although I was nervous (and it showed) for the first few months, forcing myself to test ways of starting conversations improved my confidence and boosted my career.

You might not have grown up stuttering. Still, like me, you might struggle to find the right words. The following guide gives you specific conversation starters that I’ve found successful. Use them to quickly build more successful relationships with everyone you meet.

To kick things off, we are going to start with conversation starters in professional settings and then move on to social ones.

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Conversation Starters in Professional Settings

When I first researched ways to better connect with others at work, I advised leading with a question like “Describe your perfect day.” However, after the first person that I asked looked me up and down and replied, “Alone,” I realized that going straight in with a bold question may not be the best way.

After many trials, and even more errors, I discovered the power of leading with the following type of opener:

“Sorry to interrupt. Over the last few weeks, I have been asking everyone I meet their opinion regarding this one question…”

Throughout this guide, there are a handful of bullet-proof icebreakers that you can use to lead with.

This works especially well in professional settings, as it cushions your introduction in an engaging and memorable way. Everyone likes to be asked their opinion, and chances are you’ll learn something interesting about the person, too.

Now for some specifics.

Conversation starters at a networking event

Here are a few you might use a professional meeting or networking event related to your job or the business world.

“Sorry to interrupt. Over the last few weeks, I have been asking everyone I meet their opinion regarding this one question…”

1. “Why was your best boss the best?”

2. “What one quality is mandatory to be an effective leader?”

3. “What is the greatest lesson you have learned from one of your mentors?”

4. “If you could take the stage tomorrow and give a talk about anything you wanted, what topic would you choose?”

The questions above work well in both one-on-one and group settings (all of these can start a great debate) and all of them generate more than one-word answers — aka the enemy of all conversation starters.

However, my failsafe at a networking event (which I am not the first person in saying can be uncomfortable) is the following question:

5. “Hello, sorry to bother you, but I believe we share a mutual friend in [name of person].”

The beauty of the question above is that it is very hard to walk away from and can be recycled again and again as you work your way through an event. Of course, you’ll have to do some research to use it.

A very easy way to get started with this is by checking out the event page to see who will be in attendance. Then, do a cross-reference to see if anyone interesting shares any mutual connections. Facebook and LinkedIn make this too easy. However, I cannot recommend enough verifying with your friends that they do indeed have a relationship with the person you are eager to meet. Walking up to someone and dropping an unfamiliar name can lead to an uncomfortable exchange.

Now that you are armed with a few ideas to start conversations at a networking event, let’s move onto how to initiate conversations in the office, whether sitting around the water cooler or waiting for a meeting to start.

Conversation starters in the office

In an office setting, there’s another lead you can try using:

“Recently my friends and I have been arguing about the following the topic. Would you mind being the tie-breaker?”

This is a great lead question because it serves as a sign-post that an interesting question is coming, giving you permission to ask conversations starters like:

6. “In the next five years, which skills do you think will be most in demand?”

7. “What type of job do you think would be the most beneficial for someone starting out in their career?”

8. “Is ‘follow your passion’ good or terrible advice?”

9. “Do you think most people are more productive working from home or in the office?”

All of the questions above work well because they get people talking about their own opinions, which is much more effective than going up to someone and talking about yourself. Not only that, how they respond will allow you to learn if you share similar values or interests, so you can begin to spot the small opening that can potentially lead to lasting relationships.

Now that we have a handful of ways to initiate conversations at work and networking events, let’s dig into some ways to start conversations with your peers at school.

Conversation starters at school

In these examples for an academic setting, we go back to the opener, “Sorry to interrupt. Over the last few weeks, I have been asking everyone I meet their opinion regarding this one question….”

10. “If you could read only one book for the rest of your life, what would it be?”

11. “What is the one subject that schools are not teaching, but should, and why?”

12. “No matter what you study, should public speaking be a mandatory class for all students?”

13. “If you did not have to sleep, how would you spend the extra 8 hours?”

Or you could adapt some of the questions from the work section and use them in a school setting: “Why was your best teacher the best?” or “What type of courses do you feel best prepare people for real-world work?”

These questions open the door for people to talk about things they are passionate about, such as their families, side projects and hobbies to see if your lines cross.

Speaking of common interests, the question below works as a great fail-safe when meeting new people at school:

14. “If you were not here studying, what would your normal Thursday evening look like?”

Which, again, you can also adopt for a networking event: “If you were not here tonight, what would you normally be doing on a Wednesday evening?” or even in the office, “If you did not have to work, how would you spend your time?”

About introducing yourself

You may have noticed in the list of icebreakers and conversation leads above that I never lead off by introducing myself. There is a good reason for this: most people have a hard time remembering names and hearing it first thing without any context makes this even more difficult.

So instead of leading with “Hi, my name is Michael,” I found much greater success ending the conversation by sharing my name and asking for theirs: “I really enjoyed speaking with you. I only have one more question: my name is Michael. What’s yours?”

By exchanging names at the end of a conversation, you raise the probability of both parties remembering them. Not only that, the conversation “ender” above is guaranteed to get a smile, while also opening the door for an easy transition to be made when asking for contact details if a connection is made:

Me: “I really enjoyed speaking with you. I only have one more question: My name is Michael. What’s yours?”

The person you are speaking with: “My name is Liam.”

Me: “Nice to meet you, Liam. I would love to continue this conversation at a later date. Is it cool if I connect with you over Linkedin?”

(I find LinkedIn to be great for this, as it is not as personal as other sites and seems to be the new business card.)

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Conversation Starters in Social Settings

Here are some ways to start interesting conversations in more social settings.

Some of the conversation starters below you may find cheesy, while others hit home. Your job, like anything in life, is to be like Bruce Lee and “adapt what is useful, reject what is useless and add what is specifically your own.”

Conversation starters at the gym

Starting a conversation at the gym can be tricky. However, hidden inside the lead below lies just the right mix of self-deprecating humor (which can be extremely effective when done right) as well as a subtle compliment, making it hard to engage with.

For this, I use a lead like this: “As someone who is obviously better than I am at taking care of themselves….”

15. “When starting out is consistency more important than intensity?”

16. “Is a low-carb diet the best way to lose weight?”

17. “Do you have any tips on how to stay in shape, for someone who travels a lot for work?”

18. “Is it even possible to get six-pack abs if you have a soft spot for booze?”

The conversation starters above work well with meeting new people at the gym. However, when all else fails you cannot go wrong with asking someone:

17. “Would you mind sharing with me a few hacks to stay motivated to exercise every day?”

The beauty of the gym is that everyone is taking the steps to improve their health, so immediately you have something in common. Use this to your advantage and ask them about their hard lessons learned and successes earned. You may just find you make a new friend in the process.

The lead above when meeting new people at the gym also works wonders when attending a party. However, you can also take it one step further and turn your ice-breaker into a fun guessing game.

Conversation starters at a party

Here, another lead you might use is, “As someone who is obviously great at meeting new people…”

19. “Are you in sales, by chance, or a professional speaker?”

Or a mix of compliment followed by a question: “As someone who has style….”

20. “Would you mind giving me a few tips on what to buy my sister for Christmas? She loves fashion, but as you may have noticed, I don’t.”

Is it just me or is it hard to not smile when even reading those last two examples? Just make sure you adopt the last one to what is authentic to you as an individual. The last thing you want to do is potentially start a relationship under false pretenses just to get a smile.

However, if you do not connect with the examples above, you cannot go wrong with this oldie but goodie:

20. “Hi. My name is Mike. How do you know the host?”

Much like a margarita pizza, this is a classic for a reason: it works.

Conversation starters with children

Speaking of smiles, the guessing game lead is also great for children.

The beauty of kids is they do not lie. And the smile on their faces when you play this game will tell you that you are about to make a new friend:

21. “What’s your name? Wait, don’t tell me. Is it Hulk?”

22. “What do you want to be when you grow up? Wait, don’t tell me. Let me guess. A dinosaur?”

This format not only works well with kids but also with adults. The next time you forget to break the habit of asking someone where they are from, or what they do for a living, stop yourself and finish the question with, “Wait, don’t tell me. You are wearing cowboy boots, so I am going to take a shot in the dark and say New York City.”

Like I said before, the beauty of the conversation starters and questions above is you can play a mixing and matching game with them. So let’s play a speed round in different social situations to see how they go.

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Interesting Conversation Starters in Specific Sociations

Conversation starter when on public transportation

23. “Sorry to bother you. My friends and I have been arguing about something for the last few weeks and I would love for you to be the tie-breaker: Taking off a year before starting college is a good idea, right?”

Conversation starter when speaking with the parents of your kids’ friends

24. “The last few weeks I have been asking everyone I meet this one question. Seeing that you also have kids, I would love to know what you do to effectively disconnect after work to be more present with your family?”

Conversation starters when sitting next to a celebrity

If you ever meet a celebrity, the odds are high that you will tell the story of how you met them at every dinner party for the rest of your life. However, why not start a conversation that will ensure they will talk about you for the rest of theirs? For example,

25. “As someone who has been married a few times, can you give me some advice on the best way to end one?”

I have a hard time imagining Brad Pitt not getting a kick out of that one!

But if you do not feel comfortable being that bold, you can always ask the question below to start an interesting conversation:

26. “How many years did it take before you became ‘an overnight success?’”

Conversation starter for someone sitting next to you at dinner

27. “I really admire the positive energy you have. Would you mind sharing with me your secret? No wait, let me guess. Alcohol?”

Conversation starter when waiting in line to get coffee

28. “Sorry to bother you before you have had your morning cup of energy. Growing up, my mom and I used to play a game where we guessed what people did for a living. Based on your shoes, are you a nurse by chance?”

You’ll need to adjust this one based on what you observe, but obviously, choose something innocuous. Read on for topics to avoid in any conversation opener.

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Conversation Starters to Avoid When Meeting New People

In the list of conversation starters above, you may have noticed I avoided talking about topics like race, sex, religion, money, and politics. The reason for this is not because these topics are not important. It’s because people become much more open in having a discussion if a few commonalities have first been identified.

Imagine you put 50 people in a room and start by asking them about their opinion of Trump. Unfortunately, divisions will be made and potential learning experiences will be lost. However, imagine the same situation, but instead of going straight in with a topic that can potentially divide people, you begin by asking their opinion on impactful books or by sharing career lessons or travel experiences.

These may not be the conversations that solve the world’s problems. However, they may be what opens the door for trust to be built so those conversations can take indeed take place.

In short, by asking questions that have no borders you make it that much harder for people to build borders back up.

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Ultimately, It’s About Learning from Others

Dale Carnegie left us with a million and one nuggets of wisdom during his lifetime. However, when it comes to building relationships, none more important than, “If you want to be interesting, first be interested.”

The key to the conversation starters above is they accomplish just that because they demonstrate to others you are someone who wants to learn from and about them.

However, just because you successfully started a conversation does not guarantee a successful conversation will take place.

Once you start a conversation, it is time to give your mouth a rest and activate your ears and give people your undivided attention in order to identify relevant follow-up questions. You must continue listening until you have heard the magical words signifying a connection has been made: “What about you? What do you think?”

To see this in action let’s play one last game and mash-up as many of the ideas above into one conversation. In it, I use the lead of “I am writing an article” (that’s gold for all you writers out there — carte blanche to speak to anyone):

You: “Sorry to bother you. I am writing an article for recent college graduates and have been asking everyone I meet to share with me their favorite piece of career advice. Would you mind sharing with me yours?”

New person: “Great question. If I had to narrow it down to just one I would have to say, ‘Be on time, be present, and be positive.’”

You: “Wow, that’s a belter. Let me guess. You were in the military?”

New person: “(smile) No, I wasn’t, but my dad was and growing up he used to say that those eight words were the key to reaching our goals.”

You: “I could not agree more. Especially with being present. Recently a friend of mine said to me, “Our time is not our most valuable asset, our presence is.” (Shout out to Rafael Sarandeses).

New Person: “I love that. What about you? What is your favorite piece of career advice?”

You: “Mine is a bit more cliché,`Meet as many people as you can and leave each person better than you found them.´”

New Person: “So true.”

You: “Listen, I have to run, but I really enjoyed talking with you. My name is Michael, by the way, what’s yours?”

New Person: “It was nice speaking to you also. My name is Liam.” 

You: “Great talking, Liam. If coffee people are anything, they are creatures of habit. You cool if I connect with you on Linkedin and we try and link up to continue this conversation the next time you plan to swing by here?”

Six sentences, and the result? A great new connection.

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A Rich Life of Connection

17 years have passed since I began being proactive about initiating more conversations.

Over this time my career in sales and communication has taken me all over the globe. I’m a far cry from the shy kid who had been terrified even to say his own name.

More importantly, it has played a leading role in developing relationships today with people who I could not imagine my life without.

One chance encounter, one introduction, and one conversation can change our world.

But for this change to take place, you have to be willing to put yourself out into the world and discover a way to say hello.

I have always been told that when meeting new people, it is best to leave a conversation unfinished so you have an excuse to connect at a later date.

That being said… over the last few weeks, I have been asking everyone I meet their advice regarding the best question to ask when meeting new people. I would love to know in the comments below: what is your go-to conversation starter? 

Article written by Michael Thompson for Medium

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